apparition: I've been thinking a lot about this too. I've been trying to push through some of my backlog by starting with older, smaller games. Ive mostly been sticking to old Sierra games that I can install into DOSBox on my work computer for small game time during my lunch break.
I got stuck in the Police Quest series for a couple of months because I got close to getting burned out on it but wanted to finish the series. I'm now at Police Quest 4, which is a big nostalgia hit for me and I'm still having trouble getting started.
Leucius: Best advice I was ever given was by a gog'er named KneeTheCap - he tells me whenever I get burnt out on a game or I'm just generally not feeling the gaming vibe, three things:
1) Games are a work of art
2) Never regret purchasing a game, as you are at the very least, collecting a piece of art
3) Games are meant to be FUN - if you are getting burnt out on a game, or something about a game rubs you the wrong way, put it down and move on.
I've taken these three basic ideas towards gaming, and it's helped me a lot. I'm lucky to know Knee, he's a great friend that I've leaned on heavily over the years.
Above all else, have FUN with your games. It doesn't matter if you own 5, 50, or 500. You supported a medium and artform that at one point almost didn't survive. Enjoy your hobby. Between my friends I talk to, personal introspection, and friendly advice from people in threads like this, this is what I try to live by with my hobby. I no longer look at my game collection as something to be ashamed of. People have hobbies far more expensive than mine, and considering I'm poor, it's a pretty cheap hobby to have.
Good luck!
My friend is always suffering with 2 of the last points. Whereas I've learned to game when I feel like and what I feel like, he is tortured when he goes back to an older game. He also agonize over buying new games because he has "too many" games already. He also feels like he should be playing through games as much as possible, but it won't feel fun if you have to force yourself to do it. I've tried explaining all this to him but he has always been a bit of a neurotic. Meanwhile, I'm replaying my favorite games for the umpteenth time and watch as my game library quietly expands. I'll play something new if I get bored of the old games, and that's the way I enjoy my games.
You on the other hand seem like you enjoy clearing your backlog as a challenge, so keep doing what you're doing.